Longtime vocalist Ann Caldwell takes a “why not?” approach to creative projects, even those outside of her comfort zone.
“When people say jazz, I think, okay, I’ve heard jazz. This is what jazz does. I think I can do it,” Caldwell told the Charleston City Paper.
Though she sang at home throughout her childhood, it wasn’t until her early 20s that she performed her first vocal solo. She was nine months pregnant at the time. Her daughter, Alison, was born one week later.
“After that, it was just one thing after another,” Caldwell said. “You’re walking down this hill, and then pretty soon you’re running down this hill.”
Caldwell was encouraged by her mother to audition for the 1989 production of Porgy and Bess, and she got a part in the choral group. She also nabbed her first recurring paid gig at Alice’s Fine Foods soul food restaurant downtown, increasing her visibility on the scene.
“Somebody would come in and say can you sing over here? Can you sing with the orchestra? And I’d give it a try,” she said.
In 1995, a friend suggested she link up with a local party band The David Archer Band. She didn’t yet have much experience with jazz, but she was always game for a challenge.
“I started scatting and the drummer literally knelt down and bowed in front of me,” Caldwell said.
Part of Caldwell’s distinct poignancy as a singer and performer stems from her viewpoint of the role of the vocalist as an emotional interpreter, treating each song as if it’s a conversation.
“I pay attention to what lyrics are saying and use my vocal ability to anticipate what people are looking for: a certain way you hold the note, a certain way you make them listen to it,” she said. “And that’s kind of where I go with pretty much any genre that I’ve sung.”
It’s an ethos Caldwell has carried through her myriad projects, from the jazz band Loose Fit as well as her work with local acapella spiritual group the Magnolia Singers.
Once, as a solo artist, she was tasked with performing the Japanese National Anthem for a group from Japan.
“I practiced all night,” Caldwell said of the request. “I saw how deeply respectful everybody was of that anthem — so I gleaned that. And that’s what I do. Then I take it and interpret it.”
Caldwell’s careful attention to detail paid off: “They said I captured the feeling of the song.”
Thinking through her rise to prominence in the Charleston music scene, Caldwell noted it was often challenging as a young female singer to take the lead position in a band.
“I started out as a side singer … and gradually I came into starting my own band and being the one that counts off, and tells them how fast or how long I want to sing songs, as opposed to them doing it,” she said.
In recent years she has noticed more women in the area taking control, and she mentioned being impressed by the talent of Lowcountry vocalists like Zandrina Dunning.
“I’m seeing women, young women, doing that now which I think is awesome,” Caldwell said, “because it makes the song do something different. If someone’s controlling how long you sing a song, if they shorten the song, there’s some things you can’t do. It’s changing. Women are striving to be a lot more visible, especially young women.”
During the pandemic, Caldwell shifted her focus toward storytelling, approaching new projects with the sort of calm, unassuming confidence that is her signature. She created a musical/story pairing for works of art at the Gibbes Museum of Art called “Exodus” and also presented “From Africa to the White House,” a children’s history lesson about the African American journey in the U.S.
She’s now working on a children’s book from writing she has been tinkering with for years, stashing little pieces around the house.
“I was looking at all the stacks of paper [thinking], ‘What am I going to do?’ I fixed everything in the yard. I haven’t cleaned any baseboards — I refuse to do that,” she said. “I started thinking okay, maybe I need to take my stuff out of that stack and do something with it.”
Still enthralled by performance, Caldwell is putting on a show at 4:45 p.m. March 26 at Fox Music House — her first with a full band since the pandemic. The reception starts at 4 p.m.
She and seasoned Charleton musicians pianist Richard Harris White, drummer Dave Patterson, bassist Vincent Rivers, guitarist/vocalist Roger Bellow and saxophonist Oscar Rivers are putting on a “Sentimental Journey” concert consisting of music from the ’30s, ’40s and ’50s.
She described the show as a “FUNraiser” — it’s meant to be a spirit-lifting good time.
“I will provide space for dancing,” Caldwell said. “Hopefully it will [bring] together the old and the young to enjoy music that never dies.”




